441816
CAS Number
38462-04-3Grade
Highly PurifiedMolecular Formula
C23H29ClO5Molecular Weight
420.93EU Commodity Code
38220090Shipping Temp
RTStorage Temp
-20°C(-)-Ascofuranone
3-Chloro-4,6-dihydroxy-2-methyl-5-[(2E,6E)-3-methyl-7-[(2S)-tetrahydro-5,5-dimethyl-4-oxo-2-furanyl]-2,6-octadien-1-yl]benzaldehyde;|[S-(E,E)]-3-Chloro-4,6-dihydroxy-2-methyl-5-[3-methyl-7-(tetrahydro-5,5-dimethyl-4-oxo-2-furanyl)-2,6-octadienyl]-benzaldehyde; Ascofuranone
Ascofuranone is an isoprenoid antibiotic originally isolated as a hypolipidemic substance from the phytopathogenic fungus, Ascochyta viciae by researchers at Chugai Pharmaceutical Co., Japan in 1973. Ascofuranone demonstrates antitumor activity against FM3A murine mammary, B16 melanoma and Lewis lung carcinomas. Ascofuranone increases splenic cytotoxicity and phagocytic activity of host animal cells. Ascofuranone targets c-Myc independent of p53. Ascofuranone also inhibits respiration, mitochondrial uptake and glycerol-3-phosphate dehydrogenase. Ascofuranone is active against trypanosomes.
Synonyms
3-Chloro-4,6-dihydroxy-2-methyl-5-[(2E,6E)-3-methyl-7-[(2S)-tetrahydro-5,5-dimethyl-4-oxo-2-furanyl]-2,6-octadien-1-yl]benzaldehyde; [S-(E,E)]-3-Chloro-4,6-dihydroxy-2-methyl-5-[3-methyl-7-(tetrahydro-5,5-dimethyl-4-oxo-2-furanyl)-2,6-octadienyl]-benzaldehyde; Ascofuranone
Molecular Formula
C23H29ClO5
Solubility
Soluble in Ethanol, Methanol, DMF or DMSO.
Storage and Stability
May be stored at RT for short-term only. Long-term storage is recommended at -20°C. For maximum recovery of product, centrifuge the original vial prior to removing the cap.
Intended for research use only. Not for use in human, therapeutic, or diagnostic applications.
References
1. Isolation and structure of ascofuranone and asofuranol, antibiotics with hypolipidemic activity. Sasaki H. et al. J Antibiot 1973, 26, 676|2. Antitumor and antimetastatic activity of an antibiotic, ascofuranone, and activation of phagocytes. Magae J. et al. J Antibiot 1988, XLI, 959|3. p53-independent induction of G1 arrest and p21WAF1/CIP1 expression by ascofuranone, an isoprenoid antibiotic, through downregulation of c-Myc. Jeong J-H. Mol Cancer Ther 2010, 9, 2102.|4. Yabu, Y., et al.: Parasitol. Int., 52, 155 (2003)|5. Cho, H., et al.: Carcinogenesis, 28, 1104 (2007)USBio References
No references available